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craigslist

Vacation Rentals in Chicago

  1. see also
  2. Visiting the Evanston area for 3 days or more? Check us out.
    $269
    Evanston IL
  3. Marriott's Aruba Ocean Club (July 20, 2026 to July 27, 2026)
    $2,700
    Palm Beach Aruba
  4. Wyndham Glacier Canyon at The Wilderness Waterpar11/14-16 in 3 bdrm
    $695
    north chicagoland
  5. Condo - Bradenton Florida - Seasonal Rental
    $1,500
    Bradenton
  6. Old Naples Florida resort rental. Near Beach. Jan 10th thru Jan 17th
    $1,800
    Naples
  7. Waterfront Cottages with boats
    $135
    Barryton
  8. Perfect for groups
    $135
    Chicago, IL
  9. Ideally located in West Lakeview withing walking distance to Wrigley Field
    $150
    Chicago, IL
  10. Perfect for groups
    $150
    Chicago, IL
  11. Ideally located in West Lakeview withing walking distance to Wrigley Field
    $150
    Chicago, IL
  12. Perfect for groups
    $150
    Chicago, IL
  13. JANUARY GETAWAY TO MEXICO
    $0
    Puerto Vallarta
  14. TOWNHOME FOR THANKSGIVING FAMILY GATHERING
    $0
    CHRISTMAS MOUNTAIN / WISCONSIN DELLS
  15. Modern Recent home
    $125
    Chicago
  16. Hotel rooms available discounted rates
    $0
    city of chicago
  17. Superbowl Party and Final Four Accommodations
    $1,990
    10 minutes from Grand Rapids Airport
  18. PUEBLO BONITO ROSE RESORT
    $4,000
    Chicago
  19. Condo in Chantecleer Lakes
    $1,200
    Naperville
  20. Gorgeous Top-floor 1 bed/1 bath
    $1,300
    Chicago
  21. New Years Eve and Independence Day week
    $800
    Wisconsin Dells, Wi.
  22. Perfect for groups
    $150
    Chicago, IL
  23. Condo on the beach
    $0
    7 Mile Beach
  24. Wisconsin Dells - Glacier Canyon Nov 20-22 w/10 waterpark wtbnds
    $299
    Wisconsin Dells
  25. Wisconsin Dells - Glacier Canyon Nov 23-25 w/ 4 wrtpk wristbands
    $249
    Wisconsin Dells
  26. Vacation / Temporary Furnished Luxury Rental Avail Jan and Feb 2026
    $8,500
    Libertvyille
  27. New construction elevator building
    $150
    Chicago, IL
  28. Perfect for groups
    $150
    Chicago, IL
  29. Escape Winter in Oceanfront Penthouse
    $3,995
    North Myrtle Beach
  30. Located in one of the most desired neighborhoods in Chicago
    $3,000
    Chicago
  31. Christie Lodge Timeshare Week for Sale (Avon near Vail) - $750
    $0
    Avon, CO.
  32. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 390
    $390
    Bartlett ILLINOIS 60103
  33. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  34. Furnished motel style suite, No Deposit daily $ 75.00 week;y 395.00
    $395
    Bartlett ILLINOIS 60103
  35. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 390
    $390
    Bartlett ILLINOIS 60103
  36. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 375
    $375
    Bartlett ILLINOIS 60103
  37. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  38. Wisconsin Dells - Glacier Canyon Dec 8-12 w/10 waterpark wtbnds
    $249
    Wisconsin Dells
  39. Wisconsin Dells - Glacier Canyon Dec 15-18 w/10 waterpark wtbnds
    $249
    Wisconsin Dells
  40. Wisconsin Dells - Glacier Canyon Dec 15-20 w/10 waterpark wtbnds
    $249
    Wisconsin Dells
  41. Perfect for large group
    $150
    Chicago
  42. Perfect for groups
    $135
    Chicago, IL
  43. Gold Coast Lake Michigan Corner Stidio
    $1,800
    Chicago
  44. Wisconsin Dells - Glacier Canyon Nov 20-22 w/8 waterpark wristbands
    $240
    Wisconsin Dells
  45. Modern and Well-Equipped Cabin in Minocqua, WI.
    $0
    Gurnee
  46. 5 STAR RESORT - GREAT Amenities + Full Kitchen
    $900
    WORLDWIDE
  47. 4 Bdrm Private Pool/Spa Home
    $4,000
    Palm Desert
  48. Wisconsin dells Glacier canyon
    $0
    Fredonia
  49. Smokey Mountain Fall vacatiion
    $850
    Gaitlinburg
  50. Attention snowmobilers
    $3,500
    Presque Isle
  51. rci points for sale
    $200
    fredonia
  52. Vacation home available for rent
    $3,195
    Chicago
  53. Assistance for right girl or couple
    $0
    city of chicago